KR102089683B1 - Aqueous emulsion of kabamato functionalized organopolysiloxane - Google Patents

Abstract

The present invention is a novel aqueous emulsion,
(A) A kavamato functionalized organopolysiloxane containing, on average, at least one kabamato functional Y group of the formula:
-R ^4- [NX-R ^5- ] _n NX-H
In the above formula,
X is the same or different and is a hydrogen atom
-CO-O-CHR ⁶ -CH ₂ -OH or -CO-O-CH ₂ -CHR ⁶ -OH
Is a Z radical, wherein on average one or more X radicals are Z radicals,
R ⁴ is the same or different and is a divalent Si-C-bonded hydrocarbyl radical containing 1 to 18 carbon atoms,
R ⁵ is the same or different and is a divalent hydrocarbyl radical containing 1 to 6 carbon atoms,
R ⁶ is the same or different and is a hydrogen atom or a monovalent hydrocarbyl radical containing 1 to 36 carbon atoms, wherein at least one -CH ₂ -group is a heteroatom, preferably -O- or -S- Can be substituted by,
n is 1, 2, 3 or 4;
(B) a nonionic polyethylene oxide-containing emulsifier containing at least 40 ethylene oxide units of the formula -CH ₂ -CH ₂ -O- and having an HLB value of 15 or more; And
(C) water
It includes, and having a particle size (D50) of 100 nm or less, relates to an aqueous emulsion.

Description

Aqueous emulsion of kabamato functionalized organopolysiloxane

The present invention relates to an aqueous emulsion of a kabamato functionalized organopolysiloxane, its preparation and its use in cosmetic compositions.

Silicone has long been known as a component of cosmetic compositions. This is also the case for carbamato functionalized polydiorganosiloxanes, for example as described in EP 639 369 A1. Kabamato functionalized polydiorganosiloxanes (prepared by reaction of amino-functionalized polydiorganosiloxanes with ethylene carbonate and / or propylene carbonate) used for hair conditioning in the above documents are mainly used in hair conditioner-containing compositions. It is added as an ingredient. In a clear / transparent cosmetic product, the use of unmixed polydiorganosiloxane is often excluded because the cosmetic composition often turns cloudy, and as a result, stability is lost. This should be observed especially in the case of a high amine valued polysiloxane or in the case of a polydiorganosiloxane prepared from a relatively high amine valued amino functionalized polydiorganosiloxane. This case corresponds to the example of EP 639 369 A1 (amine value> 0.5 mmol / g).

Likewise, EP 1 972 330 describes the use of a carbamato functionalized polydiorganosiloxane as a major component in cosmetic products, wherein the carbamato functionalized polydiorganosiloxane is prepared by reaction with glycerol carbonate. do.

WO 2009/150213 discloses analogous products (prepared by reaction of amino functionalized polydiorganosiloxanes with a relatively high amine number greater than 0.5 mmol / g and glycerol carbonate) for the finishing of organic fibers and textiles. .

One way to introduce organopolysiloxanes into cosmetic compositions is to provide them in the form of emulsions, especially in the form of clear / transparent microemulsions for cosmetic compositions. Microemulsions are thermodynamically stable mixtures of water (aqueous phase), oil (water miscible phase) and surfactants (solubilizer).

Microemulsions in which an oil phase is formed deterministically by polysiloxanes are known.

US 4,620,878 discloses the preparation of emulsions and microemulsions containing amino functional polydiorganosiloxanes. In the method described above, a concentrate consisting of a surfactant, a polydiorganosiloxane and a small amount of water is first prepared and diluted with water to prepare a microemulsion.

US 6,153,569 describes the use of microemulsions comprising amino functionalized polydiorganosiloxanes to obtain transparent shampoo compositions. Since it is very difficult to prepare microemulsions using a relatively low amine-valued amino-functionalized polydiorganosiloxane, a relatively high amine-valued (> 0.16 mmol / g) amino-functionalized polydiorganosiloxane is used.

If the polydiorganosiloxane is functionalized with a hydrophilic group, especially a relatively large number of hydroxyl groups, it is possible to prepare microemulsions. One example is a microemulsion of the reaction product of an amino functionalized polydiorganosiloxane with an amine value of 0.98 mmol / g and glycerol carbonate, as described, for example, in WO 2009/150213 A1. An important factor here is the level of hydroxyl groups for silicon. In the examples mentioned in WO 2009/150213 A1, the HO group is about 3.13% by weight.

The problem that has been raised is, as an aqueous emulsion of a kabamato functionalized organopolysiloxane having a small particle size, the organopolysiloxane contains only a small amount of hydroxyl groups, and the emulsion is suitable for the preparation of a clear and transparent cosmetic composition. It was about whether it was possible to provide an emulsion, which had only a very small viscosity change even if there was a viscosity change even after storage.

The above problem is solved by the present invention.

The present invention provides an aqueous emulsion comprising:

(A) a carbamato functionalized organopolysiloxane containing an average of at least one carbamatofunctional Y group of the formula:

-R ^4- [NX-R ^5- ] _n NX-H

In the above formula,

X is the same or different and is a hydrogen atom

-CO-O-CHR ⁶ -CH ₂ -OH or -CO-O-CH ₂ -CHR ⁶ -OH

Is a Z radical, wherein at least one X radical per molecule is a Z radical,

R ⁴ is the same or different and is a divalent Si-C-bonded hydrocarbyl radical containing 1 to 18 carbon atoms,

R ⁵ is the same or different and is a divalent hydrocarbyl radical containing 1 to 6 carbon atoms,

R ⁶ is the same or different and is a hydrogen atom or a monovalent hydrocarbyl radical containing 1 to 36 carbon atoms, wherein at least one -CH ₂ -group is a heteroatom, preferably -O- or -S- Can be substituted by,

n is 1, 2, 3 or 4, preferably 1;

(B) a nonionic polyethylene oxide-containing emulsifier containing more than 40 ethylene oxide units of the formula -CH ₂ -CH ₂ -O- and having an HLB value of at least 15; And

(C) As an aqueous emulsion containing water, an aqueous emulsion having a particle size (D50) of 100 nm or less is provided.

The emulsion of the present invention is preferably at least 5% by weight, more preferably at least 10% by weight, and preferably up to 50.0% by weight, more preferably up to 35% by weight, particularly preferably up to 25% by weight Includes a functionalized organopolysiloxane (A).

The emulsion of the present invention is preferably at least 0.5% by weight, more preferably at least 0.8% by weight, particularly preferably at least 1.2% by weight, and preferably up to 20% by weight, more preferably at most 15% by weight, in particular It preferably contains up to 10% by weight of a nonionic polyethylene oxide-containing emulsifier (B).

The emulsion of the present invention is preferably at least 1% by weight, more preferably at least 5% by weight, particularly at least 10% by weight, and preferably up to 94.5% by weight, more preferably up to 85% by weight, especially up to 80% by weight % Water (C).

The emulsion of the present invention preferably has a particle size (D50) of 80 nm or less, more preferably 50 nm or less, particularly preferably 40 nm or less.

The aqueous emulsion of the present invention is optionally,

(A) carbamato functionalized organopolysiloxane,

(B) a nonionic polyethylene oxide-containing emulsifier containing more than 40 polyethylene oxide units of the formula -CH ₂ -CH ₂ -O- and having an HLB value of at least 15, and

(C) as well as water,

Additional ingredients include:

(D) additional ionic or nonionic emulsifiers or mixtures thereof, each having an HLB value less than 15,

(E) a non-aqueous solvent or co-emulsifier and

(F) adjuvants, such as pH adjusting agents, salts, foam inhibitors, thickeners and / or protective colloids, preservatives, disinfectants, wetting agents, corrosion inhibitors, dyes, fragrances or mixtures thereof.

Kabamato functionalized polydiorganosiloxanes (A) have been known for a long time and are described, for example, in JP 2047371 A2.

In the composition of the present invention, it is preferable to use a kabamato functionalized organopolysiloxane (A) containing the following structural units:

M [R ¹ ₂ R ² SiO _1/2 ] and / or M ' [R ¹ ₂ (Y) SiO _1/2 ]

And

D [R ¹ ₂ SiO _2/2 ] and / or D ' [R ² (Y) SiO _2/2 ] and / or T' [(Y) SiO _3/2 ]

And optionally

T [R ¹ SiO _3/2 ] and / or

Q [SiO _4/2 ].

[However, there is one or more structural units having an average carbamato functional group Y per molecule, in which case the average one or more Y groups per molecule contains a Z radical,

here,

R ¹ is the same or different and is a monovalent Si-C-bonded hydrocarbyl radical containing 1 to 18 carbon atoms,

R ² is the same or different and is an alkoxy group of R ¹ radical or hydroxyl group -OH or formula -OR ³ (where R ³ is an optionally substituted alkyl radical having 1 to 8 carbon atoms), Y Is as defined above.]

In the composition of the present invention, it is preferred to use a carbamato functionalized polydiorganosiloxane (A) of the formula:

[R ¹ ₂ R ² SiO _1/2 ] ₂ [R ² (Y) SiO _2/2 ] _k [R ¹ ₂ SiO _2/2 ] _m (I)

Wherein R ¹ , R ² and Y are as defined above,

Here, on average, at least one Y group per molecule includes a Z radical,

m is an integer, at least 40, preferably at least 65, more preferably at least 110, and up to 1000, preferably up to 800, more preferably up to 500,

k is an integer, at least 1, preferably at least 2, and at most 15, preferably at most 10, more preferably at most 7, in which case the ratio of m to k is at least 65, preferably at least 100 , More preferably at least 130, and up to 1000, preferably up to 800, more preferably up to 600.

Optionally, it is also possible to provide a small amount of structural units T or Q to the carbamato functionalized polydiorganosiloxane (A) of formula (I).

In the kabamato functionalized organopolysiloxane (A), especially in the kabamato functionalized polydiorganosiloxane (A), it is preferably at least 5 mol%, more preferably at least 15 mol%, particularly preferably in the Y group. Is at least 20 mol%, and preferably less than 100 mol%, more preferably less than 75 mol%, particularly preferably less than 50 mol%, the N-linked X radical is not a hydrogen atom, but refers to the meaning of the Z radical. Have

This means that the amino group, preferably at least 5 mol%, and preferably less than 100 mol%, more preferably less than 50 μmol%, has been functionalized by the Z radical, ie the kabamato group.

It is also possible to use one or two or more mixtures of the kabamato functionalized organopolysiloxane (A) of the present invention.

The kabamato functionalized organopolysiloxane (A) used in the composition according to the present invention preferably comprises an amino functionalized organopolysiloxane (A ') and a cyclic carbonate containing at least one group Y' of the formula: Prepared by reaction with:

-R ^4- [NH-R ^5- ] _n NH ₂

In the above formula, R ⁴ , R ⁵ and n are as defined above.

For the production of kabamato functionalized organopolysiloxanes (A), it is preferred to use amino functionalized polydiorganosiloxanes (A ') of the formula:

[R ¹ ₂ R ² SiO _1/2 ] ₂ [R ² (Y ') SiO _2/2 ] _k [R ¹ ₂ SiO _2/2 ] _m (I')

In the above formula,

R ¹ , R ² , m and k are as defined above,

Y 'is -R ^4- [NH-R ^5- ] of the general formula _n NH ₂ Ki

Here, R ⁴ , R ⁵ and n are as defined above.

The cyclic carbonates used are preferably those having the formula:

In the above formula, R ⁶ is as defined above.

For the production of the kabamato functionalized organopolysiloxane (A), the amount of cyclic carbonate used in the prepared kabamato functionalized organopolysiloxane (A) is preferably at least 5 mol%, more preferably in the Y group. Is at least 15 mol%, particularly preferably at least 20 mol%, preferably less than 100 mol%, more preferably less than 75 mol%, particularly preferably less than 50 mol% N-linked X radicals are Z radicals It is selected to switch to.

The reaction of the amino functionalized organopolysiloxane (A ') with the carbamato functionalized organopolysiloxane (A) obtained from the cyclic carbonate produces hydroxyl groups. The amount of hydroxyl groups (% by weight of OH) in the kabamato functionalized organopolysiloxane introduced by the functionalization is preferably at least 0.002% by weight, more preferably at least 0.02% by weight, particularly preferably at least 0.03% by weight, and preferably up to 0.7% by weight, more preferably up to 0.32% by weight, particularly preferably up to 0.17% by weight.

Examples of the hydrocarbyl radical R ¹ are alkyl radicals such as methyl, ethyl, n-propyl, isopropyl, 1-n-butyl, 2-n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neo Pentyl, tert-pentyl radicals, hexyl radicals such as n-hexyl radical, heptyl radicals such as n-heptyl radical, octyl radicals such as n-octyl radical and isooctyl radicals such as 2,2,4-trimethylpentyl radical, nonyl Radicals such as n-nonyl radicals, decyl radicals such as n-decyl-rest, dodecyl radicals such as n-dodecyl radical, and octadecyl radicals such as n-octadecyl radical; Cycloalkyl radicals such as cyclopentyl, cyclohexyl, cycloheptyl and methylcyclohexyl radicals.

Preferred examples of R ¹ include methyl, ethyl, octyl and dodecyl radicals. A particularly preferred example of R ¹ is a methyl radical.

Examples of the hydrocarbyl radical R ² are radicals or hydroxyl groups as described for the R ¹ radical -OH or the formula -OR ³ (where R ³ is methyl, ethyl, n-propyl, isopropyl, 1-n- Alkoxy groups of butyl, 2-n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl), tert-pentyl radicals, hexyl radicals such as n-hexyl radicals, heptyl radicals such as n- Heptyl radicals, octyl radicals such as n-octyl radical and isooctyl radicals such as 2,2,4-trimethylpentyl radical.

Preferred examples of R ² include methyl radicals, ethyl radicals, hydroxyl groups, methoxy radicals and ethoxy radicals.

Examples of R ⁴ are divalent hydrocarbyl radicals, such as methylene group, 1,2-ethylene group, 1,3-propylene group, 1,3-butylene group, 1,4-butylene group, 1,5-pentylene group, 1,6-hexylene group is mentioned.

Particularly preferred examples include 1,3-propylene group and 1,3-butylene group.

Examples of R ⁵ are divalent hydrocarbyl radicals, such as 1,2-ethylene group, 1,3-propylene group, 1,3-butylene group, 1,4-butylene group, 1,5-pentylene group, 1,6 -Hexylene group is mentioned.

A particularly preferred example is 1,2-ethylene group.

R ⁶ is preferably a hydrogen atom, or a monovalent hydrocarbyl radical optionally substituted with -O- and having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, more preferably Alkyl or alkoxyalkyl radicals having 1 to 10 carbon atoms, especially 1 to 6 carbon atoms.

Preferred examples of Y 'radicals

-(CH ₂ ) ₂ NH (CH ₂ ) ₂ NH ₂ ,

-(CH ₂ ) ₃ NH (CH ₂ ) ₂ NH ₂ ,

-(CH ₂ ) ₃ NH (CH ₂ ) ₃ NH ₂ ,

-(CH ₂ -CH (CH ₃ ) -CH _2- ) NH (CH) ₂ NH ₂ and

-(CH ₂ ) ₄ NH (CH ₂ ) ₄ NH ₂ .

Particularly preferred examples of the Y 'radical are

-(CH ₂ ) ₃ NH (CH ₂ ) ₂ NH ₂ and

And-(CH ₂ -CH (CH ₃ ) -CH _2- ) NH (CH) ₂ NH ₂ .

The indices k and m in the formula (I ') are preferably at least 50 as measured in each case at the viscosity of the amino functionalized polydiorganosiloxane (A') used at a shear rate of 25 ° C and 10 / s. mPas, more preferably at least 100 mPas, particularly preferably at least 250 mPas, preferably in each case at a shear rate of 25 ° C. and 5 / s, preferably up to 100 000 mPas, more preferably up to 50 000 mPas , Particularly preferably selected to be up to 10 000 mPas.

The ratio of k and m is preferably the amino functionalized polydiorganosiloxane (A ') used is at least 0.025 mmol / g, more preferably at least 0.075 mmol / g, particularly preferably at least 0.1 mmol / g , And preferably up to 0.4 mmol / g, and more preferably up to 0.25 mmol / g, particularly preferably up to 0.2 mmol / g of amine value.

The reaction of the amino functionalized organopolysiloxane (A ') with cyclic carbonate reduces the amine value. Accordingly, the kabamato functionalized organopolysiloxane (A), in particular the kavamato functionalized polydiorganosiloxane (A), is preferably at least 0 mmol / g, more preferably at least 0.02 mmol / g, particularly preferably It has an amine value of at least 0.04 mmol / g, preferably up to 0.30 mmol / g, more preferably up to 0.20 mmol / g, particularly preferably up to 0.10 mmol / g.

Cyclic carbonates used in the production of kabamato functionalized polydiorganosiloxanes (A) may be commercially available or may be synthesized as described, for example, in US 3642858 A.

Generally, the cyclic carbonate used is 1,2-alkylene carbonate or alkoxyalkyl substituted ethylene carbonate.

Preferred cyclic carbonates are carbonates in which R ⁶ is a hydrogen atom or a monovalent hydrocarbyl radical optionally substituted by -O- and containing 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms. admit.

Examples thereof are ethylene carbonate, 1,2-propylene carbonate, 1,2-butylene carbonate, 1,2-pentylene carbonate, 1,2-hexylene carbonate, 1,2-octylene carbonate, 1,2-dode Silene carbonate, 3-methyl-1,2-butylene carbonate, 3-methyl-1,2-pentylene carbonate, 3-ethyl-1,2-pentylene carbonate, 4-methyl-1,2-pentylene carbonate , 5-methyl-1,2-hexylene carbonate, 3-methoxy-1,2-propylene carbonate, 3-ethoxy-1,2-propylene carbonate, 3-n-propoxy-1,2-propylene carbonate , 4-methoxy-1,2-butylene carbonate, 4-ethoxy-1,2-butylene carbonate, S-methoxy-3-butylene carbonate, 5-methoxy-1,2-heptylene carbonate Can be mentioned.

Preferred cyclic carbonates include ethylene carbonate, 1,2-propylene carbonate, and 3-methoxy-1,2-propylene carbonate.

A particularly preferred cyclic carbonate is 1,2-propylene carbonate.

The nonionic polyethylene oxide-containing emulsifier (B) used in the aqueous emulsion of the present invention preferably has an HLB value of 16 or more, more preferably 17 or more, while at the same time preferably 45 or more, preferably 50 Those having a content of ethylene oxide units of no more than, and preferably no more than 600, more preferably no more than 400, particularly preferably no more than 250.

The HLB value (HLB means hydrophilic-lipophilic balance) mainly describes the hydrophilic and lipophilic components of the nonionic surfactant. The HLB value can be calculated for nonionic surfactants according to Hans-Dieter Doerfler, Grenzflaechen- und Kolloidchemie [Interface and Colloidal Chemistry], VCH, Weinheim, 1994, p. 198, as follows:

In the above formula, M _l is the molar mass of the lipophilic component in the molecule, and M is the molar mass of the whole molecule. The coefficient 20 is a freely chosen scaling factor.

Examples of the nonionic polyethylene oxide-containing emulsifier (B) of the present invention include:

-Alkyl polyglycol esters, preferably alkyl radicals of 8 to 20 carbon atoms, for example Steareth-100 (9005-00-9), Talloweth-50, Talloweth-80 (61791-28-4), Trideceth -50 (24938-91-8),

-Carboxylic acid polyglycol esters, especially fatty acid polyglycol esters, preferably carboxylic acid esters of 8 to 20 carbon atoms, for example PEG-75 oleate, PEG-200 oleate, PEG-300 monooleate, PEG- 400 oleate, PEG-150 laurate, PEG-400 laurate, PEG-75 stearate, PEG-100 stearate, PEG-600 stearate, PEG-150 distearate,

Ethoxylated sorbitan fatty acid esters such as PEG-40 sorbitan oleate, PEG-80 sorbitan laurate,

-Ethoxylated castor oil or hydrogenated variants, for example (named according to the INCI nomenclature) PEG 75 castor oil or PEG200 castor oil or PEG-80 hydrogenated castor oil, PEG-100 hydrogenated castor oil, PEG-200 hydrogenated castor oil,

-Ethoxylated fatty amines such as PEG-100 tallowalkyl-amine (61791-44-4), PEG-40 stearylamine,

-Ethoxylated glyceryl fatty acid carboxylates such as PEG-40 glyceryl laurate, PEG-200 glyceryl stearate, PEG-200 glyceryl tallowate, PEG-200 hydrogenated glyceryl palmate,

14 600) (시그마-알드리치(Sigma-Aldrich)에서 시판됨), -Block copolymers of ethylene oxide and propylene oxide units (polyalkylene block polymers such as so-called poloxamers), for example PEG-PPG-PEG block polymers Pluronic® F-108 (HLB>24; M _n

14 600) (commercially available from Sigma-Aldrich),

15　000) (시그마-알드리치에서 시판됨).-A copolymer of ethylene oxide and propylene oxide units crosslinked through an ethylenediamine core (referred to as poloxamine), for example Tetronic 1107 (HLB value: 24; M _n

15 000) (commercially available from Sigma-Aldrich).

The nonionic polyethylene oxide-containing emulsifier (B) of the present invention may consist of one of the above-mentioned emulsifiers, or a mixture of two or more of the above-mentioned emulsifiers, in which case they are used in pure form or water or organic. It can be used as a solution of one or more emulsifiers in a solvent.

Additional components used in the emulsion of the present invention

(D) Additional ionic or nonionic emulsifiers or mixtures thereof, such as combinations of nonionic and cationic emulsifiers each having an HLB value less than 15.

Examples of anionic emulsifiers include:

1. Alkyl sulfates, especially those having a chain length of 8 to 18 carbon atoms, having 8 to 18 carbon atoms in the hydrophobic radical, and 1 to 30 ethylene oxide (EO) or propylene oxide (PO) units Having an alkyl and an alkali ether sulfate.

2. Sulfonates, especially alkylsulfonates having 8 to 18 carbon atoms, alkylarylsulfonates having 8 to 18 carbon atoms, tauride, sulfosuccinic acid and monovalent having 4 to 15 carbon atoms Esters and monoesters with alcohols or alkylphenols (the alcohols or alkylphenols may optionally be ethoxylated in 1 to 30 EO units).

3. Alkali metal and ammonium salts of carboxylic acids having 8 to 20 carbon atoms in alkyl, aryl, alkaryl or aralkyl radicals.

4. Partial phosphoric acid esters and alkali metal and ammonium salts thereof, especially alkyl- and alkaryl phosphates having 8 to 20 carbon atoms in organic radicals, having 8 to 20 carbon atoms in alkyl or alkaryl radicals, 1 Alkyl ether or alkali ether phosphate having 30 to EO units.

Examples of nonionic emulsifiers include:

5. Polyvinyl alcohol containing 5% to 50%, preferably 8% to 20% of vinyl acetate units, with a degree of polymerization of 500 to 3000.

6. Alkyl polyglycol ethers, preferably those having 3 to 30 EO units and alkyl radicals of 8 to 20 carbon atoms.

7. Alkylaryl polyglycol ethers, preferably those having 5 to 30 EO units and 8 to 20 carbon atoms in the alkyl and aryl radicals.

8. Ethylene oxide / propylene oxide (EO / PO) block copolymers, preferably those having 8 to 30 EO / PO units.

9. Addition product of ethylene oxide or propylene oxide with an alkylamine having an alkyl radical of 8 to 22 carbon atoms.

10. Fatty acids having 6 to 24 carbon atoms.

11.The general formula R * -OZ _O (where R * is a straight-chain or branched, saturated or unsaturated alkyl radical having an average of 8-24 carbon atoms, and Z _O is an average o = 1-10 hexoses or Alkyl polyglycosides of oligoglycoside radicals having pentoose units) or mixtures thereof.

12. Natural substances and derivatives thereof, such as lecithin, lanolin, saponin, cellulose; Cellulose alkyl ethers and carboxyalkyl celluloses (the alkyl groups each have 4 or fewer carbon atoms).

13. Linear organic (poly) siloxanes containing polar groups, in particular linear organic (poly) siloxanes containing elements O, N, C, S, P, Si, especially up to 24 carbon atoms and / or 40 Those having an alkoxy group containing the following EO and / or PO groups.

Examples of cationic emulsifiers include:

14. Salts of primary, secondary and tertiary fatty amines having 8 to 24 carbon atoms with acetic acid, sulfuric acid, hydrochloric acid and phosphoric acid.

15. Alkylpyridinium, alkylimidazolinium and alkyloxazolinium salts, especially those wherein the alkyl chain has up to 18 carbon atoms, especially halides, sulfates, phosphates and acetates.

16. Quaternary alkyl- and alkylbenzeneammonium salts, especially those wherein the alkyl group has 6 to 24 carbon atoms, especially halides, sulfates, phosphates and acetates.

Examples of amphoteric emulsifiers include:

17. Amino acids with long chain substitution, such as N-alkyldi (aminoethyl) glycine or N-alkyl-2-aminopropion salts.

18. Betaines such as N- (3-acylamidopropyl) -N, N-dimethylammonium salts with alkyl radicals and alkylimidazolium betaines with C ₈ -C ₁₈ -acyl radicals.

Preferred emulsifiers are nonionic emulsifiers, especially the alkyl polyglycol ethers listed in item 6 above. The emulsifier (D) can be used alone or in the form of a mixture of two or more of the above-mentioned emulsifiers, in which case they can be used in pure form or as a solution of one or more emulsifiers in water or an organic solvent. have.

The emulsion of the present invention is preferably at least 0.5% by weight, more preferably at least 1% by weight, particularly at least 2% by weight, and preferably up to 20% by weight, more preferably up to 15% by weight, especially up to 10% by weight Emulsifier (D) in an amount of%.

Additional components used in the emulsion of the present invention

(E) It may be a non-aqueous solvent or a co-emulsifier.

The emulsion of the present invention is preferably at least 0.1% by weight, more preferably at least 0.4% by weight, particularly at least 0.8% by weight, and preferably up to 20% by weight, more preferably up to 15% by weight, especially up to 10% by weight (E) Non-aqueous solvent or co-emulsifier in an amount of%.

The non-aqueous solvent (E) that can be used in the aqueous emulsion of the invention is derived from the group of alkanolamines or glycol ethers, for example monovalent or polyhydric alcohols. Examples of solvents are ethanol, n- or i-propanol, butanol, such as 1-butanol, 2-butanol or 2-methyl-2-propanol, pentanol, such as 1-pentanol, 2-pentanol or 3-pentanol , Hexanol, such as 1-hexanol, 2-hexanol or 3-hexanol, heptanol, such as 1-heptanol, 2-heptanol, 3-heptanol or 4-heptanol, octanol, such as 1- Octanol, 2-octanol, 3-octanol or 4-octanol, glycol, propanediol, butanediol, such as butane-1,2-diol or butane-1,3-diol, hexanediol, such as hexane-1, 2-diol or 2-methylpentane-2,4-diol, octanediol, such as 2-ethylhexane-1,3-diol or octane-1,2-diol, glycerol, diglycol, propyl- or butyldiglycol, Ethylene glycol methyl ether, ethylene glycol ethyl ether, ethylene glycol propyl ether, ethylene glycol mono-n-butyl ether, diethylene glycol methyl ether, diethylene glycol ethyl ether, diethylene Recall mono-n-butyl ether, propylene glycol methyl ether, propylene glycol ethyl ether, propylene glycol propyl ether, propylene glycol n-butyl ether, propylene glycol tertiary butyl ether, methoxytriglycol, ethoxytriglycol, butoxy Triglycol, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, 1-butoxyethoxy-2-propanol or 3-methyl-3-methoxybutanol, 1-aminobutane, 2-aminobutane, 2- Amino-2-methylpropane, 1-aminopentane, 2-aminopentane, 1-aminohexane, 1-aminoheptane and 1-aminooctane; Ethyl acetate, propyl acetate, isopropyl acetate, butyl acetate, isobutyl acetate, pentyl acetate, isopentyl acetate and hexyl acetate; Methyl propionate, ethyl propionate and tertiary butyl propionate; Methyl butyrate, ethyl butyrate, propyl butyrate and butyl butyrate; 2-butanone, 2-pentanone, 3-pentanone, 4-methyl-2-pentanone, 2-hexanone, 3-hexanone, 2-heptanone, 3-heptanone, 4-heptanone, 5 -Methyl-3-heptanone, 2-octanone and 3-octanone and mixtures of these auxiliary surfactants.

Examples of preferred non-aqueous solvents or co-emulsifiers (E) are the 1-alkanols of the examples given above with C ₅ to C ₈ chains, the alkanediols of the examples given above with C ₄ to C ₈ chains, glycerol, propyl acetate, butyl acetate And pentyl acetate, 2-pentanone and the ethylene glycol, propylene glycol, dipropylene glycol or diethylene glycol monoalkyl ethers shown above.

Particularly preferred non-aqueous solvents or coemulsifiers (E) are 1-pentanol, 1-hexanol, 1-octanol, propanediol, butane-1,3-diol, hexane-1,2-diol, 2-ethylhexane -1,3-diol, octane-1,2-diol, glycerol, diethylene glycol methyl ether, diethylene glycol ethyl ether, diethylene glycol mono-n-butyl ether, propylene glycol methyl ether.

In addition, polyalkylene glycols as co-emulsifiers, such as polyethylene glycol (e.g. PEG600, PEG1000 or PEG6000) or polypropylene glycol (e.g. PPG2000), polyalkylene block polymers with HLB values less than 15, such as so-called poloxamers ( Block copolymers of ethylene oxide and propylene oxide units), e.g. PEG-PPG-PEG block polymers Pluronic® L-31, PEG-PPG-PEG block polymers Pluronic® L-61, PPG-PEG-PPG block polymers Pluronic® 17R4, PPG-PEG-PPG Pluronic® block polymer 31R1 (HLB <7 in each case) (commercially available from Sigma-Aldrich) or poloxamine with an HLB value of less than 15 (ethylene oxide cross-linked via ethylenediamine core and oxidation It is also possible to use copolymers of propylene units), for example Tetronic 701 or Tetronic 90R4 (HLB <7 in each case) (commercially available from Sigma-Aldrich).

Additional components used in the emulsion of the present invention

(F) auxiliaries such as pH adjusting agents, salts, foaming inhibitors, thickeners and / or protective colloids, preservatives, disinfectants, wetting agents, corrosion inhibitors, dyes, fragrances or mixtures thereof.

The pH adjusting agents usable herein include all known acids or alkalis, provided that their use should not be prohibited for related or environmental reasons or for consumer protection reasons.

The acid used may function to set the desired pH, or it may form an acid addition salt of the carbamato functionalized polydiorganosiloxane (A) with the amino-containing radical (Y).

Examples of the inorganic acid capable of reacting with the aforementioned amino-containing radical (Y) include, for example, hydrochloric acid, perchloric acid, sulfuric acid, sulfurous acid, nitric acid, nitrous acid, hydrofluoric acid, phosphoric acid, diphosphoric acid and polyphosphoric acid. Examples of suitable carboxylic acids are formic acid, acetic acid, propionic acid, butanoic acid, citric acid, trichloracetic acid, dichloracetic acid and chloroacetic acid, trifluoroacetic acid, cyanoacetic acid, phenylacetic acid, benzoic acid, m- and p-nitrobenzoic acid, oxalic acid , Malonic acid and lactic acid.

Acetic acid and formic acid are particularly preferred.

In the context of the present invention, pH is measured using electrodes at 20 ° C. according to US Pharmacopeia USP 33.

Examples of salts (electrolytes) include, among others, those selected from the group of inorganic salts, and it is also possible to use a variety of different salts. Preferred cations include alkali metals and alkaline earth metals; Preferred anions include halide and sulfate. From the viewpoint of production, it is preferable to use sodium acetate or sodium chloride for the aqueous emulsion of the present invention.

Examples of foam inhibitors include soap, paraffin or silicone oil.

Examples of preservatives are methylisothiazolinone, chloromethylisothiazolinone, benzylisothiazolinone, phenoxyethanol, methylparaben, ethylparaben, propylparaben, butylparaben, isobutylparaben, alkali metal benzoate, alkali metal Sorbate, iodopropynyl butyl carbamate, benzyl alcohol and 2-bromo-2-nitropropane-1,3-diol.

The emulsification of the carbamato functionalized polydiorganosiloxane (A) of the present invention using the nonionic polyethylene oxide-containing emulsifier (B) of the present invention is a carbamato functionalized polydiorganosiloxane (A) in water (C). ) Is performed by strongly mixing with emulsifier (B), optionally emulsifier (D), optionally non-aqueous solvent or co-emulsifier (E), optionally with additional adjuvant (F). A stable emulsion is formed in which the kabamato functionalized polydiorganosiloxane (A) is present in finely divided form.

The emulsification operation for the production of an aqueous emulsion of the kabamato functionalized polydiorganosiloxane (A) of the present invention is preferably at least 10 ° C, more preferably at least 15 ° C, and preferably up to 80 ° C, more preferably It is carried out at a temperature of up to 70 ° C.

The increase in temperature is preferably achieved through the introduction of mechanical shear energy required for the emulsification process. An increase in temperature is not necessary to promote any chemical process. Further, the method of the present invention is preferably performed at ambient atmospheric pressure, but may also be performed at higher or lower pressures.

The manufacturing method can be continuous or batchwise.

Techniques for preparing organopolysiloxane emulsions are known. Thus, strong mixing and dispersion can be effected with a rotor-stator stirrer device, colloid mill, high pressure homogenizer, microchannel, membrane, jet nozzle or the like, or by ultrasonic. Homogenization equipment and processes are described, for example, under the entry "Emulsion" in Ullmann's Encyclopedia of Industrial Chemistry, CD-ROM edition 2003, Wiley-VCH Verlag.

The method of mixing the components used in the preparation of the emulsion of the present invention is not very important and can be performed in various orders. However, according to components (A), (B), optionally (D), optionally (E) and optionally (F), preferred procedures can occur, which must be confirmed for each individual case.

For example, the initial charge may include component (A) and optionally acid (F '), followed by addition of emulsifier (B) and optionally (D) and optionally co-emulsifier (E), followed by dispersant water ( C) and optionally further adjuvants (F) are introduced. In most cases, in the emulsifying apparatus, the initial charge comprises as part of the dispersant water (C) an emulsifier (B), optionally an emulsifier (D) and optionally an auxiliary emulsifier (E) and optionally an acid (F '), It has been found advantageous to introduce component (A) and further components into the resulting mixture.

The present invention

In a cosmetically acceptable medium, preferably in water,

One or more hair conditioners and

There is further provided a cosmetic composition comprising one or more aqueous emulsions of the present invention.

The present invention further provides a method of treating keratin fibers, preferably hair, using the cosmetic composition of the present invention.

Preferably, the composition is a cosmetic composition for cleaning and care of hair. Examples of the composition for the cleaning and care of hair include hair shampoo, rinse-off conditioner, hair tonic, hair mask, hair serum, hair foam, hair styling spray, hair cream, hair gel, hair oil, hair fluid ( hair end) and hair dyes.

In this context, the term "care" keeps keratin fibers in their original form, thereby preventing the effects of external influences (eg, chemical reactions with time, light, temperature, pressure, contaminants and other reactive compounds that come into contact with the product). It means reducing or avoiding effects, eg aging, contamination, discoloration, or even improving the desired positive properties of keratin fibers. Examples of these are: improved softness (flexibility) and smoothness, reduced combing force, improved gloss, color, color protection, reduced electrostatic charge, thermal deformation or hydrophobicization of hair And the protective properties of the city.

The aqueous emulsion of the present invention is preferably 0.1 to 40% by weight, more preferably 0.2 to 30% by weight, particularly preferably 0.4% by weight, in each case based on the total weight of the composition in the composition. % To 20% by weight.

The composition in which the aqueous emulsion of the present invention is used may be in the form of a W / O emulsion (oil-in-water emulsion), O / W emulsion (oil-in-water emulsion) or a complex emulsion.

Preferably, the cosmetically acceptable medium in the cosmetic composition is water.

The composition in which the aqueous emulsion of the present invention is used is preferably a composition having a translucent or transparent appearance.

These preferred compositions are transparent or translucent microemulsions with droplet diameters ranging from about 0.01 μm to about 0.1 μm.

In contrast, in a single emulsion, in one phase there is a second phase of finely dispersed droplets (water droplets in W / O or lipid vesicles in O / W emulsion) covered by the emulsifier shell. The droplet diameter of the standard emulsion ranges from about 1 μm to about 50 μm. This "macro emulsion" is milky white and opaque, without the addition of additional colorants. Even finer “macro emulsions” with droplet diameters ranging from about 0.1 μm to about 1 μm are bluish white and opaque without the addition of additional colorants.

Only micelles and molecular solutions with a particle diameter of less than about 0.01 μm have a clear and transparent appearance.

The cosmetic composition in which the aqueous emulsion of the present invention is used includes one or more hair conditioners, which will hereinafter simply be referred to as conditioners. [K. Krummel, Stephane Chiron, J. Jachowicz, Chapter 14, in: "The Chemistry and Manufacture of Cosmetics", Volume II, Formulating, Third Edition by Mitchell L. Schlossmann, 2000, p. 359-396, the conditioner refers to a cosmetic ingredient that deforms the hair surface to affect the properties of the hair. Cosmetic compositions comprising a conditioner, for better disentanglability, to reduce wetting and dry combing, for hair care, to prevent electrostatic charge, through the hair and through the hair surface For smoother glide, to improve hair shine, to maintain hair color fastness, to reduce hair breakage, to maintain hair style and additional cosmetic properties associated with natural and healthy hair, It is used to modify or improve softness.

Compositions in which the aqueous emulsions of the present invention are used improve one or more of the aforementioned effects.

An example of a conditioner and its INCI name is described in the "International Cosmetic Ingredient Dictionary and Handbook" of the American Personal Care Product Council (eds.). Available references include the World Wide Web-based ["wINCI" Web Based International Cosmetic Ingredient Dictionary and Handbook] (http://online.personalcarecouncil.org/jsp/Home.jsp) or [the International Cosmetic Ingredient Dictionary and Handbook, 13th Edition, The Personal Care Products Council (formerly Cosmetic, Toiletry, and Fragrance Association (CTFA)), 2010.

A preferred example of conditioner is a cationic polymer. These are understood to mean pendant or terminal cationic groups which can be converted to cationic groups by ionization or polymers containing pendant or terminal groups. It is preferred to use cationic polymers containing quaternary ammonium groups.

Examples of cationic polymers which are preferably used are published under the "polyquaternium" name section of the [International Cosmetic Ingredient Dictionary and Handbook], and each polymer is identified by a separate numerical code, for example polyquaternium-1. do.

Further examples of cationic polymers are derivatives of modified polysaccharides with quaternary ammonium groups, for example polymers with the INCI name Cassia hydroxypropyltrimonium chloride, derivatives of modified cellulose and / or starch. , Quaternary ammonium derivatives of the propylene glycol ether-modified Cyamopsis tetragonoloba (GUA) gum, for example INCI name guar hydroxypropyltrimonium chloride, or hydroxyethyl cellulose and trimethyl Polymeric quaternary ammonium salts of reaction products with ammonium substituted epoxides, such as cellulose, 2-hydroxyethyl 2- (2-hydroxy-3- (trimethylammonium) propoxy) ethyl 2-hydroxy-3- ( Trimethylammonium) propyl ether chloride, such as cellulose, 2-hydroxyethyl 2-hydroxy-3- (trimethylammonium) propyl ether, chlora De, such as cellulose, 2-hydroxyethyl 2-hydroxy-3- (trimethylammonium) propyl ether, chloride, such as cellulose, 2- [2-hydroxy-3- (trimethylammonium) propoxy] ethyl ether, chloride (INCI name is polyquaternium-10).

Further examples of cationic polymers include the following cationic polymers containing quaternary ammonium groups: acrylic acid polymer derivatives, acrylic acid copolymer derivatives, methacrylic acid derivatives and methacrylic acid copolymer derivatives, for example the INCI name The polymer which is this polyquaternium-37 is mentioned.

Further examples of cationic polymers include copolymers containing quaternary ammonium groups formed from dimethyldiallylammonium chloride and acrylic acid, for example polymers with the INCI name polyquaternium-22.

Further examples of cationic polymers are copolymers containing quaternary ammonium groups formed from vinylpyrrolidone, vinylimidazole and derivatives of vinylimidazole and methacrylic acid, for example the polyquaternium with the INCI name- And a polymer of 86.

Further examples of cationic polymers include copolymers containing quaternary ammonium groups formed from acrylamide and dimethyldiallylammonium chloride, for example polymers with the INCI name polyquaternium-7.

A further example of a cationic polymer is a copolymer containing a quaternary ammonium group formed from the reaction product of diethyl sulfate and vinylpyrrolidone and dimethylaminoethyl methacrylate, for example the INCI name is polyquaternium-11 And polymers.

The composition in which the aqueous emulsion of the present invention is used is preferably 0.01% to 5% by weight, more preferably 0.05% to 4% by weight, particularly preferably 0.10% by weight, in each case based on the total weight of the composition. % To 3% by weight of cationic polymer.

A further preferred example of conditioner is a cationic surfactant. Examples of cationic surfactants which are preferably used correspond to the substances listed in items 14. to 16. under the example of cationic emulsifiers. Examples include cetyltrimethylammonium salt or behenyltrimethylammonium salt. Examples of anionic counterions that may be present include chloride, bromide, and methosulfate. The INCI names of cationic surfactants that are preferably used are, for example, cetrimonium chloride, cetrimonium methosulfate, behentrimonium chloride, behentrimonium metosulfate, steartrimonium bromide.

The composition in which the aqueous emulsion of the present invention is used is preferably 0.1% to 7% by weight, more preferably 0.15% to 6% by weight, particularly preferably 0.2% by weight based on the total weight of the composition. % To 5% by weight of cationic surfactant.

A further example of conditioner is a non-polymeric quaternary ammonium compound. It is understood to mean a non-polymeric ammonium compound which is present in cationic form or which can be converted to a cationic group by ionization. Examples of non-polymeric quaternary ammonium compounds which are preferably used are N- [3- (dimethylamino), which has an INCI name of distearyldimonium chloride, dimethyldioctadecylammonium chloride, and an INCI name of stearamidopropyl dimethylamine. Propyl] -octadecaneamide, or a compound whose INCI name is dicocoylethyl hydroxyethylmonium methosulfate or quaternium-87.

Further preferred examples of conditioners include organopolysiloxanes and organopolysiloxane copolymers other than the kavamato functionalized polydiorganosiloxane (A) present in the aqueous emulsions of the present invention. The organopolysiloxane may be in the form of an oil, wax, gum or resin, or in the form of an emulsion.

Examples of such organopolysiloxanes other than carbamato functionalized polydiorganosiloxanes (A) include:

Cyclic organopolysiloxanes of the formula [R * ₂ SiO] _x ;

(Wherein x is an integer from 4 to 8)

A straight-chain organopolysiloxane of the general formula R * ₃ SiO [R * ₂ SiO] _y SiR * ₃ or HOSiR * ₂ O [R * ₂ SiO] _y SiR * ₂ OH; And

(Wherein y is an integer from 1 to 2000)

Resinous organopolysiloxanes of the general formula R * _t SiO _{(4-t) / 2} (where each R * has the definition given above for R ¹ or Y ', and t is 0, 1, 2 or 3).

Organopolysiloxane resins are formed from M, D, T and / or Q units, likewise combinations in which D and T units predominate or consist solely of, for example, combinations in which M and Q units predominantly or consist solely of them, wherein D And in the case of a resin in which T units predominate or are formed solely from them, T units are preferably present in a molar ratio of T / [M + D + T + Q] of 0.45 to 1, more preferably 0.55 to 1.0, and In all cases, the number of M and Q units is preferably 0, and in the case of an organopolysiloxane resin in which the M and Q units predominate or are formed solely, the Q units are preferably 0.25 to 0.9, more preferably 0.35 to 0.7. Is present in a molar ratio of Q / [M + D + T + Q], and the number of D and T units in both cases is preferably 0.

Examples of the organopolysiloxane when present in the form of an oil include polydimethylsiloxane having a viscosity of 0.65 to 2 000 000 mPas (25 ° C) and having the INCI names disiloxane and dimethicone.

Further examples of organopolysiloxanes when present in the form of an oil or wax include functionalized organopolysiloxanes, for example polyalkylsiloxanes in which one or more alkyl radicals differ from methyl, for example stearyl dimethicone with the INCI name , Organopolysiloxanes that are cetyl dimethicone or C26-28 alkyl dimethicones, or, for example, polyarylsiloxanes and polyarylalkylsiloxanes, for example the INCI name is phenyl trimethicone, trimethylsiloxyphenyl dimethicone or dimethylphenyl Organopolysiloxanes which are dimethicones, or organopolysiloxanes containing organofunctional radicals such as, for example, aminopropyl, aminopropyl-aminoethyl, aminopropyl-aminoisobutyl radicals, for example with the INCI name amodimethicone Phosphorus organopolysiloxane, or, for example, an organic pole containing polyethylene glycol or polyalkylene glycol radicals Siloxanes, for example, INCI name may be mentioned are PEG-12 dimethicone, PEG / PPG-25,25- dimethicone or cetyl PEG / PPG-15/15 butyl ether dimethicone in the organopolysiloxane.

Further examples of organopolysiloxanes include silicone resins with the INCI name trimethylsiloxysilicate or polymethylsilsesquioxane.

The composition in which the aqueous emulsion of the present invention is used is preferably 0.1% by weight to an organopolysiloxane and an organopolysiloxane copolymer other than the carbamato functionalized polydiorganosiloxane (A) based on the total weight of the composition. 40% by weight, preferably 0.2% by weight to 30% by weight, particularly preferably 0.3% by weight to 20% by weight.

Further preferred examples of conditioners include fatty acid esters and fatty alcohols.

Examples of fatty alcohols include alcohols having a C ₈ -C ₂₈ carbon chain, such as fatty alcohols, 1-octadecanol with the INCI name stearyl alcohol, 1-hexadecanol with the INCI name cetyl alcohol, or the INCI name. And fatty alcohols such as tearyl alcohol, myristyl alcohol, capryl alcohol, lauryl alcohol, decyl alcohol, and oleyl alcohol.

In addition to conditioning properties, fatty alcohols also fulfill the organizational and thickening effects in cosmetic compositions.

Further examples of fatty acid esters are esters of fatty acids whose INCI name is palmitic acid, oleic acid, linoleic acid, linolenic acid, caprylic acid, myristic acid, stearic acid, for example, the INCI name is isopropyl palmitate, ethylhexyl palmitate, And fatty acid esters that are isopropyl myristate and isopropyl stearate.

The composition in which the aqueous emulsion of the present invention is used is preferably 0.1 to 15% by weight, more preferably 0.3 to 12% by weight, particularly preferably 0.5% by weight, in each case based on the total weight of the composition. Fatty acid esters and fatty alcohols in an amount of% to 10% by weight.

Additional preferred examples of conditioners include natural or synthetic oils and waxes.

Examples of preferred oils and waxes include hydrocarbons containing straight or branched, saturated or unsaturated C ₄ -C ₆₀ carbon chains, such as isododecane with the INCI name, hydrated polyisobutylene, hydrated polydecene, paraffin And oils and waxes that are isoparaffins.

Further examples of preferred oils and waxes include carnauba wax, beeswax, wool wax, microcrystalline wax, jojoba oil, rice bran oil, calendula oil, sunflower oil, soybean oil, coconut oil, olive oil and almond oil.

The composition in which the aqueous emulsion of the present invention is used is preferably 0.1% to 10% by weight, more preferably 0.2% to 7% by weight, particularly preferably 0.3% by weight based on the total weight of the composition. Oil and wax in an amount of from 5% to 5% by weight.

Further preferred examples of conditioners include panthenol, lipids such as ceramides, proteins and hydrolyzed proteins such as hydrolyzed collagen, hydrolyzed wheat protein and hydrolyzed silk.

The hair conditioners used are preferably those selected from the following group:

Cationic polymer,

Cationic surfactant,

Non-polymeric quaternary ammonium compounds,

Organopolysiloxane and organopolysiloxane copolymers other than the carbamato functionalized polydiorganosiloxane (A) present in the aqueous emulsion of the present invention,

Fatty acid esters and fatty alcohols,

Natural or synthetic oils and waxes and

Panthenol, lipids, proteins and hydrolyzed proteins, and mixtures thereof.

Optionally, the composition is an additional standard cosmetic additive, such as surfactants, thickeners, gelling agents, film formers, wetting agents, UV filters, pearlescent pigments, vitamins, antioxidants, caffeine, anti-dandruff activity Ingredients or preservatives, or mixtures thereof.

Examples of additional additives commonly used in cosmetics and their INCI names are described in the American Cosmetic Association's "International Cosmetic Ingredient Dictionary and Handbook".

Optionally, the composition comprises additional standard cosmetic additives, such as surfactants.

Examples of surfactants common in cosmetics are also described in K. Schrader, A. Domsch, Cosmetology-Theory and Practice, Volume II, pages II-8 to II-22, Verlag fuer chemische Industrie, 2005, examples of emulsifiers are described below.

Examples of anionic surfactants which are preferably used correspond to the substances listed in items 1. to 3. under the example of anionic emulsifiers.

The INCI name of anionic surfactants that are preferably used is, for example, sodium lauryl sulfate, ammonium laureth sulfate, sodium laureth sulfate, disodium 2-sulfolaurate, disodium lauryl sulfosuccinate or Sodium laureth-sulfosuccinate.

The composition in which the aqueous emulsion of the present invention is used is preferably 1% to 30% by weight, more preferably 5% to 25% by weight, particularly preferably 7% by weight, in each case based on the total weight of the composition. % To 20% by weight of anionic surfactant.

Examples of nonionic surfactants which are preferably used correspond to the substances listed in items 5. to 13. below, examples of nonionic emulsifiers. The INCI names of nonionic surfactants which are preferably used are, for example, coco glucoside, lauryl glucoside, decyl glucoside, PEG-40 hydrogenated castor oil, polysorbate 80 or PEG-7 glyceryl coco Eight.

The composition in which the aqueous emulsion of the present invention is used is preferably 1% by weight to 15% by weight, more preferably 2% by weight to 12% by weight, particularly preferably 3% by weight based on the total weight of the composition. % To 10% by weight of nonionic surfactant.

Examples of amphoteric surfactants which are preferably used correspond to the substances listed in items 17. to 18. under the example of nonionic emulsifiers. Further preferred examples include compounds of the alkylamido betaine, alkyl amphoacetate and alkyl amphopropionate classes. The INCI names of nonionic surfactants that are preferably used are, for example, cocamidopropyl betaine, cetyl betaine, cocamide MEA, cocamide DEA, cocamide MIPA, sodium cocoamphoacetate and sodium cocoamphopro. Cypionate.

The composition in which the aqueous emulsion of the present invention is used is preferably 1% by weight to 15% by weight, more preferably 2% by weight to 12% by weight, particularly preferably 3% by weight based on the total weight of the composition. Amphoteric surfactant in an amount of% to 10% by weight.

Optionally, the composition comprises additional standard cosmetic additives, such as thickeners.

Examples of thickeners which are preferably used include modified polysaccharides such as starch, cellulose, gum arabic and guar gum, for example polymers with the INCI name of cellulose gum, guar gum, xanthan gum or cassia gum.

Further examples of thickeners include hydrophobically modified nonionic cellulose derivatives, such as cellulose derivatives with the INCI name hydroxyethylcellulose.

Additional examples of thickeners include crosslinked acrylic and methacrylic acid polymers, and derivatives of crosslinked acrylic or methacrylic acid polymers, for example polymers with the INCI name carbomer.

Additional examples of thickeners include agents that achieve a thickening effect with a surfactant. Examples include monoglycerides of fatty acids, mono / diglycerides of ethoxylated fatty acids, and ethoxylated fatty alcohols. The INCI name of the preferred thickener used to achieve a thickening effect with a surfactant is PEG-120 methyl glucose dioleate, PEG-150 distearate, myristyl glycol, PEG-200 glyceryl palmitate, laureth- 4 or PEG-200 glyceryl palmitate.

Additional examples of thickeners include salts, for example, salts with the INCI name sodium chloride.

The composition in which the aqueous emulsion of the present invention is used preferably comprises a thickener in an amount of 0.1 to 10% by weight in each case based on the total weight of the composition.

Optionally, the composition comprises additional standard cosmetic additives, such as a coating agent.

A preferred example of the coating agent is a polymer.

Examples of film forming polymers that are preferably used are described in the American Cosmetic Association's "International Cosmetic Ingredient Dictionary and Handbook".

Preferred coating film forming polymers include acrylic acid polymer derivatives, acrylic acid copolymer derivatives, methacrylic acid derivatives and methacrylic acid copolymer derivatives. Examples of preferred anionic polymers include copolymers of vinyl acetate and one or more acrylic or methacrylic acid monomers and esters thereof, such as polymers with the INCI name acrylate / VA copolymer.

Examples of preferred coating film forming polymers include copolymers of vinylpyrrolidone and one or more acrylic or methacrylic acid monomers and esters thereof, such as polymers with the INCI name acrylate / VP copolymer.

Examples of preferred coating film forming polymers include tertiary butylacrylamide and copolymers of one or more acrylic or methacrylic acid monomers and their esters, for example polymers with the INCI name acrylate / 3 tertiary butylacrylamide copolymer.

Further examples of preferred film forming polymers include copolymers of vinyl acetate, crotonic acid and vinyl neodecanoate monomers, for example polymers with the INCI name VA / crotonate / vinyl neodecanoate copolymer.

Further examples of preferred film forming polymers are copolymers of vinyl acetate, crotonic acid and vinyl neodecanoate monomers and vinylsilicone, for example with the INCI name crotonic acid / vinyl C8-C12 isoalkyl ester / VA / bis-vinyl And polymers that are dimethicone copolymers.

The composition in which the aqueous emulsion of the present invention is used is preferably 0.1 to 15% by weight, more preferably 0.2 to 10% by weight, particularly preferably 0.3% by weight, in each case based on the total weight of the composition. % To 7% by weight.

Optionally, the composition comprises additional standard cosmetic additives, such as wetting agents.

Examples of the wetting agent preferably used include glycerol, sorbitol, xylitol, polyethylene glycol, propane-1,2-diol, propane-1,3-diol or polypropylene glycol.

The composition in which the aqueous emulsion of the present invention is used is preferably 0.1% to 10% by weight, more preferably 0.2% to 8% by weight, particularly preferably 0.3% by weight based on the total weight of the composition. % To 6% by weight.

Optionally, the composition comprises additional standard cosmetic additives, such as pearlizing agents.

Examples of the brightener preferably used include pearlescent pigment or glycol distearate.

The composition in which the aqueous emulsion of the present invention is used is preferably 0.1% to 7% by weight, more preferably 0.2% to 6% by weight, particularly preferably 0.3% by weight based on the total weight of the composition. % To 5% by weight.

The present invention adds a method of preparing a cosmetic composition, preferably a transparent cosmetic composition, by mixing one or more aqueous emulsions of the invention with one or more hair conditioners and optionally additional standard cosmetic additives in a cosmetically acceptable medium. To provide.

Each of the components may be mixed with each other in a high temperature / high temperature, high temperature / low temperature or low temperature / low temperature method.

The aqueous emulsion of the present invention is preferably added to the preparation of the cosmetic composition of the present invention at a temperature of up to 50 ° C, more preferably at a temperature of up to 40 ° C, particularly preferably at a temperature of up to 35 ° C. It is preferably added at a temperature of at least 5 ° C, preferably at a temperature of at least 10 ° C.

In the examples described below, all numbers for parts and percentages are by weight, unless stated otherwise.

Unless otherwise stated, the examples described below are performed at ambient atmospheric pressure, i.e., about 1000 hPa and room temperature, i.e., about 20 ° C, or at an established temperature for mixing of reactants at room temperature without further heating or cooling.

"MCR 302" flow meter (Anton Paar) according to DIN EN ISO 3219: 1994 and DIN 53019, using a cone-plate system (CP50-2 cone) with an opening angle of 2 ° Viscosity). The equipment was zero-adjusted using Normal oil 10000 from Physikalisch-Technischen Bundesanstalt [German National Metrology Institute]. The measurement temperature is 25.00 ° C +/- 0.05 ° C and the measurement time is 3 minutes. The number of viscosities is the arithmetic mean of individual measurements performed independently. The measurement uncertainty for dynamic viscosity is 1.5%. The shear rate gradient is chosen as a function of viscosity and is given individually for each viscosity number.

The amine value indicates how much KOH (mmol) corresponds to 1 g of the measurement substance. The amine value is measured according to DIN 16945-version 1989-03.

^{The 1} H NMR spectrum is recorded as a solution in CDCl ₃ on a Bruker Avance 500 NMR spectrometer ( ¹ H NMR sample head with 5 mm selectivity) using a measurement frequency of 500.13 MHz.

Evaluations were performed as known to those skilled in the art and described in the following literature: ["Ueber die ¹ H-, ¹³ C- und ²⁹ Si-NMR chemischen Verschiebungen einiger linearer, verzweigter und cyclischer Methyl-Siloxan-Verbindungen" [On the ¹ H, ¹³ C and ²⁹ Si Chemical Shifts of Some Linear, Branched and Cyclic Methylsiloxane Compounds], G. Engelhardt, H. Jancke; J. Organometal. Chem. 28 (1971), 293-300]; ["Chapter 8-NMR spectroscopy of organosilicon compounds", Elizabeth A. Williams, The Chemistry of Organic Silicon Compounds, 1989 John Wiley and Sons Ltd, 511-533].

The particle size was measured on a Zetasizer Nano-S particle sizer (manufactured by Malvern) (software version 6.01) using dynamic light scattering (Mie measurement). For this purpose, the emulsion was diluted to 0.5% by weight using filtered and degassed water. Recorded values are always based on the D (50) value. D (50) should be considered as the volume average particle diameter, with 50% of the total particles measured being smaller than the provided D (50) value.

Example:

Example 1: Carbamato functionalized polydimethylsiloxane 1

1000.0 g of the reaction-terminated copolymer consisting of aminoethylaminopropylmethylsiloxane and dimethylsiloxane units having a viscosity of 4320 mPas and an amine value of 0.135 mmol / g (at 25 ° C. and a shear rate of 10 1 / s) is nitrogen atmosphere First, a 2000 ml three neck flask was charged first, and 3.62 g of propylene carbonate was added. The reaction mixture is stirred at 50 ° C for 2 hours and 60 ° C for 2 hours. After cooling, a clear product 1 of viscosity 6200 mPas (at 25 ° C. and a shear rate of 10 1 / s) is obtained. ^{The 1} H NMR spectrum shows the degree of functionalization associated with carbamate of 25% of all available amine groups and hence the hydroxyl group of 0.058% by weight. Kabamato functionalized polydimethylsiloxane 1 has an amine value of 0.10 mmol / g.

Example 2: Carbamato functionalized polydimethylsiloxane 2

1000.0 g of the reaction-terminated copolymer consisting of aminoethylaminopropylmethylsiloxane and dimethylsiloxane units having a viscosity of 4320 mPas and an amine value of 0.135 mmol / g (at 25 ° C. and a shear rate of 10 1 / s) is nitrogen atmosphere First, a 2000 ml three neck flask was charged first, and 7.24 g of propylene carbonate was added. The reaction mixture is stirred at 50 ° C for 2 hours and 60 ° C for 2 hours. After cooling, a clear product 1 of viscosity 9480 mPas (at 25 ° C. and a shear rate of 10 1 / s) is obtained. ^{The 1} H NMR spectrum shows the degree of functionalization associated with carbamate of 47% of all available amine groups and thus 0.107% by weight hydroxyl groups. Kabamato functionalized polydimethylsiloxane 2 has an amine value of 0.07 mmol / g.

(Comparative) Example V3: Amino functionalized polydimethylsiloxane V3

This ended the reaction of 3- (2-aminoethylamino) propylmethylsiloxy and dimethylsiloxy units, with an amine value of 0.13 mmol / g and a viscosity of 3900 mPas (at 25 ° C. and a shear rate of 10 1 / s). Copolymer V3 .

Example 4: Emulsion E1 of carbamato functionalized polydimethylsiloxane 1

The Ultra-Turrax T 50 emulsifying device (Janke & Kunkel / IKA) was first sold under the trade name Imbentin T / 060 (Kolb), 12.0 g of isotridecyl hexaethoxylate, Rewoderm LI 520-70 (Evonik). Filled with commercially available 7.5 g PEG-200 hydrogenated glyceryl palmate (HLB>19; 200 ethylene oxide units) and 8.0 g demineralized water. To induce a relatively stiff and hard phase as a preliminary emulsion, 30.0 g of kabamato functionalized product 1 is added at one time at a shear rate of 4000 rpm. 2.3 g of 80% acetic acid is added and the mixture is diluted with 90.93 g of demineralized water under low shear to obtain the desired emulsion. The emulsion is preserved with 1.35 g of 2-phenoxyethanol. The result is a colorless, transparent, pale blue, free-flowing emulsion E1 with a particle size D (50) of 32 nm. The emulsion is homogeneous and stable after storage at room temperature for 6 hours.

Example 5: Emulsion E2 of carbamato functionalized polydimethylsiloxane 2

The kabamato functionalized polydimethylsiloxane 2 is emulsified in the same manner as in Example 4. The result is a colorless, transparent, pale blue, free-flowing emulsion E2 , having a particle size D (50) of 30 nm as well. The emulsion is homogeneous and stable after storage at room temperature for 6 hours.

Example 6-10 Emulsion E3 consisting of kavamato functionalized polydimethylsiloxane 2 with different emulsifiers and amounts of emulsifier To E7

The emulsions described below are prepared in the same manner as described in Example 4.

The following emulsifier / emulsifier amounts were used:

Example 6:

12.0 g of isotridecyl hexaethoxylate commercially available under the trade name Imbentin T / 060 (Kolb)

3.75 g of PEG-200 hydrogenated glyceryl palmate commercially available under the trade name Rewoderm LI 520-70 (Evonik) (HLB> 19; 200 ethylene oxide units)

3.75 g glycerol

The result is a free-flowing emulsion E3 that is colorless, transparent and light blue in color with a particle size D (50) of 21 nm.

Example 7:

12.0 g of isotridecyl hexaethoxylate commercially available under the trade name Imbentin T / 060 (Kolb)

2.25 g of PEG-200 castor oil (50% aqueous solution) commercially available under the trade name Crorasol G-1300 (Croda) (HLB = 18.1; 200 ethylene oxide units)

The result is a transparent, pale blue instant free-flowing emulsion E4 , with a particle size D (50) of 25 nm.

Example 8:

12.0 g of isotridecyl hexaethoxylate commercially available under the trade name Imbentin T / 060 (Kolb)

7.25 g of PEG-200 castor oil (50% aqueous solution) commercially available under the trade name Cirrasol G-1300 (Croda) (HLB = 18.1; 200 ethylene oxide units)

The result is a transparent, bluish, instant free-flowing emulsion E5 with a particle size D (50) of 22 nm.

Example 9:

12.0 g of isotridecyl hexaethoxylate commercially available under the trade name Imbentin T / 060 (Kolb)

3.45 g of PEG-100 stearate commercially available under the trade name Sympatens-BS / 1000G (Kolb) (HLB = 18.8; 100 ethylene oxide units)

The result is an instant free-flowing emulsion E6 that is transparent, blue-colored, with a particle size D (50) of 28 nm.

Example 10:

12.0 g of isotridecyl hexaethoxylate commercially available under the trade name Imbentin T / 060 (Kolb)

7.50 g of PEG-80 sorbitan laurate commercially available under the trade name Tween 28 (Croda) (HLB = 19.1; 80 ethylene oxide units)

The result is a transparent, bluish, instant free-flowing emulsion E7 with a particle size D (50) of 22 nm.

(Comparative) Example 11:

Emulsion CE1 of kavamato functionalized polydimethylsiloxane 2 CE1

The kabamato functionalized polydimethylsiloxane 2 is emulsified in the same manner as in Example 4. However, the emulsifiers used are commercially available under the trade name Sympatens ALM / 040 (Kolb), 12.38 g of laureth-4 (HLB = 9.7; 4 ethylene oxide units) and under the trade name Sympatens ALM / 230 G (Kolb). 7.13 g of laureth-23 (HLB = 16.9, but 23 ethylene oxide units). The result is a whitish, cloudy free-flowing emulsion VE1 with a particle size D (50) of 112 nm.

Comparative Example 11 is a non-ionic polyethylene oxide-containing emulsifier having a content of less than 40 polyethylene oxide units is used, even when the HLB value is more than 15, the particles having a particle size of 100 nm or less It has been shown that it is impossible to obtain an emulsion of the invention.

(Comparative) Example 12:

Emulsion VE2 of amino functionalized polydimethylsiloxane V3

6.5 g of isotridecyl pentaethoxylate, 20.0 g of amino functionalized polydimethylsiloxane V3 , 2.9 g of glycerol, marketed under the trade name (BASF) of Lutensol TO 5 using an LDV 1 dissolver (PC Laborsystem) , 0.12 g of 80% acetic acid, 0.19 g of N-morpholinomethyl-triethoxysilane and 70 g of water are used to prepare an emulsion having an average particle size (D50) of 20 to 50 nm. 0.13 g of 2-phenoxyethanol is mixed into the emulsion.

Test method for evaluating the effectiveness of a cosmetic composition:

The application properties of the cosmetic composition and the effects associated with its combing force and softness were evaluated for Caucasian human hair. All hair tress are cleaned prior to use. For this purpose, tresses are left in a solvent mixture of equal parts of acetone, ethanol, isopropanol and demineralized water for 24 hours. After removing the solvent mixture, the tresses are thoroughly washed with demineralized water. Thereafter, each tress was washed with 3 mL of ammonium lauryl sulfate solution (25% concentration) STEPANOL (R) ALS 25 (manufactured by STEPAN Company) and rinsed with demineralized water until no more bubbles were visible (at least 2 minutes). . After basic cleaning, condition the tress at 23 ° C. and 60% air humidity for at least 12 hours before further use.

Measurement of combing force:

The combing force of wet and dry hair is measured using a tress (head damage class B, 2 pulls) of damaged Kogasus hair having a weight of 2 g and a length of 20 cm manufactured by Kerling International Haarfabrik GmbH. The combing force was measured using an Instron 3343 tensile compression tester [Y.K. Kamath and Hans-Dietrich Weigmann, J. Soc. Cosmet. Chem., 37, 111-124, 1986]. First, wet and dry combing forces are measured over the measurement section of the untreated tress. Thereafter, the tress is treated with the cosmetic composition according to the invention and the force entering during combing is measured. The recorded measurement is the amount of reduction (work) in combing force over the measurement interval that occurs between the treated and untreated heads. Calculate the average of the three tress. The reduction in combing force is reported as a percentage.

Flexibility (softness):

The measuring principle for measuring the hydrophobicity of hair follows the detailed description given in DE 10 2010 020 192. The softness of the hair was measured using a tress (head damage class B, 2 pulls) of damaged Kogasus hair having a weight of 2 g and a length of 20 cm, manufactured by Kerling International Haarfabrik GmbH. Hair softness in the dry state was measured by correlating the required tensile forces with the parameters of the flexural stiffness and surface roughness of the hair bundle using an Instron 3343 tensile compression tester. These two parameters are consequently correlated with hair flexibility. For this purpose, untreated tresses were clamped into a measuring device consisting of five rods facing each other. The shape of the tress at this starting position is a double-S type. After this preparation, the tress is pulled from the measuring device in one direction and the required force over the measuring section is evaluated as work. Thereafter, the tress is treated with the cosmetic composition of the present invention, and the force required to pull the tress through the measuring device in the measuring section is measured. The recorded measurement is the amount of reduction (in days) of the tensile force over the measurement interval that occurs between the treated and untreated heads. The reduction in the high percentage of tensile force (work) corresponds to good flexibility, i.e., high flexibility. Calculate the average of the three tress.

Shampoo use washing process:

0.1 g of shampoo per gram of hair is applied to the cleaned damp hair. Massage the shampoo in the direction of the hair tip for 30 seconds. Then, rinse for 30 seconds with complete demineralized water flowing through the tress, and use a coarse-toothed comb to release the tangle. The above procedure is repeated twice. In the last round, the rinse process is extended to 60 seconds. The tress is then dried at 60% air humidity and a temperature of 23 ° C. for at least 12 hours.

All numbers indicated in parts below are by weight.

Examples 13A-13B:

Cosmetic composition: shampoo

Examples described later show cosmetic compositions comprising emulsions E1 to E2 of Examples 4 to 5. The active content of the organopolysiloxane in the cosmetic composition is 0.66%.

Manufacturing instructions:

Guar hydroxypropyltrimonium chloride is dispersed in water and the mixture is heated to 75 ° C. Then, lauryl polyglucose, lauryl glucoside, glycol distearate and PEG-150 distearate are added. After stirring at 75 ° C. for 5 minutes, the solution is cooled to 35 ° C. while gradually stirring. Upon reaching the target temperature, emulsion E1 (similar procedure for emulsion E2 ), citric acid, cocamidopropyl betaine and preservatives methylchloroisothiazolinone, methylisothiazolinone are added, and the mixture is brought to room temperature. Let cool.

The comparative composition VF3 used is the cosmetic composition of Table 1. Rather than emulsions E1 to E2 , 5.0 parts of emulsion VE2 are introduced into the composition.

The viscosity of the obtained cosmetic compositions F1 to F2 and VF3 is measured immediately after production and after 12 days.

As shown in Table 2 below, the use of the emulsions E1 and E2 of the present invention in cosmetic compositions F1 and F2 has a decrease in viscosity of the composition over time, resulting in only a slight decrease even if damaged. In contrast, for the comparative composition VF3 in which an amino functionalized polydimethylsiloxane other than the carbamato functionalized polydimethylsiloxane was used, a more pronounced decrease in viscosity is evident. Therefore, the cosmetic compositions F1 and F2 comprising the emulsions E1 and E2 of the present invention have higher stability.

Example 14:

Cosmetic composition: shampoo

The example to be described later shows a cosmetic composition F4 comprising the emulsion E2 of Example 5. The active content of the organopolysiloxane in the cosmetic composition is 2%.

Manufacturing instructions:

Guar hydroxypropyltrimonium chloride is dispersed in water and the mixture is heated to 75 ° C. Sodium laureth sulfate, cocamide MIPA, glycol distearate and PEG-150 distearate are then added. After stirring at 75 ° C. for 5 minutes, the solution is cooled to 35 ° C. with gentle stirring. Upon reaching the target temperature, emulsion E2, cocamidopropyl betaine and preservatives methylchloroisothiazolinone and methylisothiazolinone are added and the mixture is cooled to room temperature. Finally, sodium chloride is added with stirring.

Comparative Example:

The cosmetic composition of Table 3 without emulsion E2 , that is, a silicone-free shampoo base, is used as the comparative composition VF5 .

Table 4 shows the measured values for the parameters of dry combing force, wet combing force and softness in the hair treated with the cosmetic composition F4 of the present invention and the cosmetic composition VF5 other than the present invention, as compared with untreated hair. Results are included.

Table 4 shows that the use of the emulsion E2 of the present invention in cosmetic composition F4 resulted in a marked improvement in management properties. The use of emulsion E2 of the present invention has been extended in dry and wet hair, resulting in a reduction in combing force. The reduction in drying and wet combing when treated with the composition F4 of the present invention was much greater than when treated with the composition VF5 other than the present invention. In addition, the flexibility of the hair in the case of treatment with the composition F4 of the present invention was also improved compared to the case of the treatment with the cosmetic composition VF5 of the present invention, which does not contain the emulsion of the present invention.

Examples 15A and 15B:

Cosmetic composition: transparent shampoo

Examples to be described later show a cosmetic composition comprising the emulsion E1 of Example 4 and the emulsion E2 of Example 5. The active content of the organopolysiloxane in the cosmetic composition is 0.5%.

Manufacturing instructions:

The polyquaternium-10 is dispersed in water and the mixture is heated to 70 ° C. with stirring. Then sodium laureth sulfate and cocamide MEA are added. The mixture is cooled to 35 ° C. with gentle stirring, and then cocamidopropylbetaine and preservatives methylchloroisothiazolinone and methylisothiazolinone are added. Thereafter, emulsion E1 or emulsion E2 previously diluted with water is added. Sodium chloride is added to adjust the viscosity of the shampoo to a target point of about 10 000 mPas.

After treating damaged Caucasian hair with shampoos F6 and F7 of Examples 15A and 15B, a softer feel was felt compared to untreated hair.

Examples 16A-16G:

Cosmetic composition: rinse conditioner 16A-16G

Examples to be described later show cosmetic compositions F8 to F14 according to Table 6 including emulsions E1 to E7 of Examples 4 to 10. The active content of the organopolysiloxane in the cosmetic composition is 0.5% to 2%.

The raw materials listed in Table 6 are available under the following trade names:

1) Hydroxyethylcellulose: Tylose ^® H 4000 P2, Shin-Etsu Chem. Co.

2) Cetyl alcohol: Cetyl alcohol, Merck KGaA

3) Polysorbate 80: Tween ^TM 80, Croda GmbH

4) Behentrimonium chloride: Genamin ^® KDMP, Clariant GmbH

5) Stearamidopropyl Dimethylamine, Incromine ^TM SB, Croda GmbH

6) Stearyl alcohol: Stearyl alcohol Merck KGaA

7) Citric Acid: Citric Acid, Sigma

8) Tetrasodium EDTA: EDETA® B powder, BASF Corporation

9) Phenoxyethanol, ethylhexylglycerin: Euxyl PE 9010, Schuelke & Mayr

Manufacturing instructions:

First, water is charged and heated to 75 ° C. while stirring. In this process, 1.2 parts of hydroxyethylcellulose are added. When reaching 65 ° C., 0.5 parts of stearamidopropyl dimethylamine, 1 part of polysorbate 80, 3 parts of stearyl alcohol, 1 part of cetyl alcohol and 1.8 parts of behentrimonium chloride are added. The mixture is stirred until it reaches 75 ° C. to make the ingredients dissolved. Then, the mixture is cooled. Upon cooling, 0.2 parts of citric acid and 0.2 parts of tetrasodium EDTA are added. At 35 ° C, 0.9 parts of phenoxyethanol and ethylhexylglycerin are added. While stirring was continued, the emulsion of the examples was added. The composition is homogenized with stirring for 15 minutes.

After treatment of damaged Caucasian human hair using the rinse conditioners F8 to F14 of Examples 16A to 16G, a softer feel was felt compared to the untreated hair.

Claims (15)

As an aqueous emulsion,
(A) A carbamato functionalized organopolysiloxane containing an average of at least one carbamatofunctional Y group of the formula:
-R ^4- [NX-R ^5- ] _n NX-H
In the above formula,
X is the same or different and is a hydrogen atom or the formula
-CO-O-CHR ⁶ -CH ₂ -OH or -CO-O-CH ₂ -CHR ⁶ -OH
Is a Z radical, wherein at least one X radical per molecule is a Z radical,
R ⁴ is the same or different and is a divalent Si-C-bonded hydrocarbyl radical having 1 to 18 carbon atoms,
R ⁵ is the same or different and is a divalent hydrocarbyl radical having 1 to 6 carbon atoms,
R ⁶ is the same or different and is a hydrogen atom or a monovalent hydrocarbyl radical having 1 to 36 carbon atoms,
n is 1, 2, 3 or 4,
However, in the carbamato functionalized organopolysiloxane (A), the N-linked X radical of less than 50 mol% in the Y group is not a hydrogen atom and has the above meaning of the Z radical,
The kabamato functionalized organopolysiloxane (A) has a hydroxyl group of up to 0.7% by weight and is characterized by having an amine value of up to 0.3 mmol / g,
(B) A nonionic polyethylene oxide-containing emulsifier containing more than 40 ethylene oxide units of the formula -CH ₂ -CH ₂ -O-, having an HLB value of 15 or greater, and selected from the group consisting of:
Alkyl polyglycol ether,
Carboxylic acid polyglycol esters,
Ethoxylated sorbitan fatty acid ester,
Hydrogenated variants of ethoxylated castor oil or ethoxylated castor oil,
Ethoxylated fatty amines,
Ethoxylated glyceryl fatty acid carboxylate,
Block copolymer of ethylene oxide and propylene oxide units referred to as poloxamers, and
A copolymer of ethylene oxide and propylene oxide units crosslinked through an ethylenediamine core called poloxamine, and
(C) water
An aqueous emulsion comprising a particle size (D50) of 100 nm or less as measured as described above. The aqueous emulsion of claim 1, wherein the used kabamato functionalized organopolysiloxane (A) is a kabamato functionalized polydiorganosiloxane of the formula:
[R ¹ ₂ R ² SiO _1/2 ] ₂ [R ² (Y) SiO _2/2 ] _k [R ¹ ₂ SiO _2/2 ] _m (I)
In the above formula,
R ¹ is the same or different and is a monovalent Si-C-bonded hydrocarbyl radical having 1 to 18 carbon atoms,
R ² is the same or different and is a R ¹ radical or a hydroxyl group -OH or an alkoxy group of the formula -OR ³ , wherein R ³ is an optionally substituted alkyl radical having 1 to 8 carbon atoms,
Y is as defined in claim 1,
Here, the average of at least one Y group per molecule is the formula
-CO-O-CHR ⁶ -CH ₂ -OH or -CO-O-CH ₂ -CHR ⁶ -OH
Is a Z radical, wherein R ⁶ is as defined in claim 1,
m is an integer, 40 or more to 1000 or less,
k is an integer, 1 to 15,
The ratio of m to k is 65 or more and 1000 or less. The aqueous emulsion according to claim 1 or 2, wherein R ⁶ is a methyl radical. According to claim 1 or claim 2, In the carbamato functionalized organopolysiloxane (A), 5 mol% or more of the N-linked X radical in the Y group is not a hydrogen atom, the meaning of the Z radical of the formula Aqueous emulsion characterized by having:
-CO-O-CHR ⁶ -CH ₂ -OH or -CO-O-CH ₂ -CHR ⁶ -OH
In the above formula, R ⁶ is as defined in claim 1. delete delete The emulsifier (B) according to claim 1 or 2, wherein the nonionic polyethylene oxide-containing emulsifier (B) contains more than 40 ethylene oxide units of the formula -CH ₂ -CH ₂ -O- and has an HLB value of 15 or more. Aqueous emulsion characterized by being selected from the group of:
An alkyl polyglycol ether having an alkyl radical of 8 to 20 carbon atoms,
The carboxylic acid polyglycol ester used is a fatty acid polyglycol ester,
The ethoxylated sorbitan fatty acid ester used is PEG-40 sorbitan oleate, PEG-80 sorbitan laurate, or mixtures thereof,
The hydrogenated modifications of ethoxylated castor oil or ethoxylated castor oil used include PEG 75 castor oil or PEG200 castor oil or PEG-80 hydrogenated castor oil, PEG-100 hydrogenated castor oil, and PEG-200 hydrogenated Castor oil, or mixtures thereof,
The ethoxylated fatty amine used is PEG-100 tallow alkylamine (61791-44-4), PEG-40 stearylamine, or mixtures thereof,
The ethoxylated glyceryl fatty acid carboxylates used are PEG-40 glyceryl laurate, PEG-200 glyceryl stearate, PEG-200 glyceryl tallow and PEG-200 hydrogenated glyceryl palmate. The method of claim 1, wherein the cover Mato functionalized organopolysiloxane (A) is, the "amino-functionalized organopolysiloxane (A containing 'and R ⁶⁾ group Y of the formula above average one per molecule of claim 1, wherein Chemical formula as defined in

An aqueous emulsion characterized by being prepared by reacting a cyclic carbonate of:
-R ^4- [NH-R ^5- ] _n NH ₂
Here, R ⁴ , R ⁵ and n are as defined in claim 1. The aqueous emulsion of claim 8, wherein the amino functionalized organopolysiloxane (A ') used is an amino functionalized polydiorganosiloxane (A') of the formula:
[R ¹ ₂ R ² SiO _1/2 ] ₂ [R ² (Y ') SiO _2/2 ] _k [R ¹ ₂ SiO _2/2 ] _m (I')
In the above formula,
R ¹ , R ² , m and k are as defined in claim 2,
Y 'is as defined in claim 8. The aqueous emulsion of claim 8, wherein the amino functionalized organopolysiloxane (A ') used has an amine value of up to 0.4 mmol / g. As a cosmetic composition,
Among the mediums that are acceptable for cosmetic use,
One or more hair conditioners, and
One or more aqueous emulsions as claimed in claim 1 or 2 or prepared according to claim 8 or 10.
Cosmetic composition comprising a. The cosmetic composition according to claim 11, wherein the hair conditioner used is selected from the following group:
Cationic polymer,
Cationic surfactant,
Non-polymeric quaternary ammonium compounds,
Organopolysiloxane and organopolysiloxane copolymers other than the kabamato functionalized polydiorganosiloxane (A) present in the aqueous emulsion,
Fatty acid esters and fatty alcohols,
Natural or synthetic oils and waxes, and
Panthenol, lipids, proteins and hydrolyzed proteins and mixtures thereof. 12. The cosmetic composition according to claim 11, which comprises an additional standard cosmetic additive selected from the following group:
Surfactants,
Thickener, gelling agent,
Film former,
Wetting Agent,
UV filter,
Pearlizing agent,
vitamin,
Antioxidant,
Caffeine,
Anti-dandruff active ingredient,
Preservatives, and
Mixtures of these. An aqueous emulsion of one or more carbamato functionalized organopolysiloxanes as claimed in claims 1 or 2 or prepared according to claims 8 or 10, in one or more conditioners cosmetically acceptable medium and optionally additional standards. A method for producing a cosmetic composition by mixing with a cosmetic additive. A method of treating keratin fibers using a cosmetic composition as claimed in claim 11.